Grilled Cheese Bites With Tomato Soup Recipe

Sauté aromatics

Heat 1 tbsp olive oil in a medium saucepan over medium heat. Add the diced onion and a pinch of salt and cook, stirring occasionally, until translucent and soft, about 6–8 minutes. Add the minced garlic and cook 30–45 seconds until fragrant.

Build tomato base

Stir in 3 tbsp tomato paste and cook 1–2 minutes to caramelize slightly. Add the canned crushed tomatoes and 1 cup stock, scraping any brown bits from the pan. Bring to a gentle simmer.

Season and simmer

Add 1 tsp sugar, 1 tsp dried oregano, chopped basil leaves, 1 tsp salt, 1 tsp black pepper and 1/4 tsp red pepper flakes (if using). Reduce heat to low and simmer, partially covered, for 15 minutes to let flavors meld.

Finish with cream and blend

Stir in 1 cup heavy cream and warm through (do not boil). Remove from heat and use an immersion blender to puree until smooth, or carefully transfer to a blender and puree in batches. Taste and adjust salt, pepper, or sugar as needed. Keep warm on very low heat while preparing the grilled cheese bites.

Prepare bread and cheese

Grate the sharp cheddar and mozzarella and combine in a bowl. In a small bowl, mix 3 tbsp softened butter with 2 tbsp mayonnaise, 1 tsp Dijon mustard and 1 tsp freshly ground black pepper until smooth. Lightly dust each bread slice with a thin dusting of the 2 tbsp flour (this helps absorb excess moisture and create a better seal).

Assemble sandwiches

Spread the butter-mayo mixture evenly on one side of each bread slice (this will be the outside that contacts the pan). Place 6 slices, buttered side down, on a work surface. Divide the cheese mixture evenly among them (about 2/3 cup cheese per sandwich), spreading to edges but leaving a small rim. Top each with a second slice of bread, buttered side up. Press gently and use a knife to seal the edges by running it along the seam (the flour helps the edges stick).

Cook and cut

Heat a large skillet or griddle over medium-low to medium heat. When hot, place sandwiches in the skillet (work in batches if needed). Cook slowly, 3–4 minutes per side, until deep golden brown and the cheese is melted — press gently with a spatula to encourage even browning. Transfer to a cutting board and let rest 1 minute, then cut each sandwich into 4 equal bite-sized squares using a sharp serrated knife or sandwich cutter. Keep warm in a low oven (200°F / 95°C) on a baking sheet while finishing remaining sandwiches.

Optional broil for crispness

For extra-crispy tops, arrange cut bites on a baking sheet, brush lightly with a little extra-virgin olive oil, and broil 1–2 minutes until edges are crisp — watch carefully to avoid burning.

Spoon the warm tomato soup dipping sauce into a shallow serving bowl or individual ramekins. Arrange grilled cheese bites on a platter around the bowl or on a board for dipping.

Garnish the soup with torn basil leaves and an optional drizzle of extra-virgin olive oil. Serve immediately while bites are warm and cheese is gooey.